Enterprise Account Executive (AI)

Location: Remote, but must be based in Chicago, United States

Salary: $250,000–$300,000 OTE annually

Company

Glean develops an AI-powered Work AI platform with enterprise search, an AI Assistant, scalable AI agents, SaaS connectors, flexible LLM support, and APIs.

What you will do

• Source and close net-new logos within an assigned enterprise territory.
• Navigate complex organizations and identify executive sponsors and internal champions.
• Research customer objectives and lead value-driven sales cycles.
• Develop sales strategies, generate pipeline, and deliver predictable bookings and ARR revenue.
• Collaborate with sales engineers, BDRs, product managers, executives, and engineers to advance opportunities and ensure customer success.
• Create ROI and business justification reports and run POCs against defined business success criteria.

Requirements

• 6+ years of closing sales experience with a record of top performance.
• Experience closing complex deals and selling into complex enterprise organizations.
• Experience selling technical SaaS and cloud-based software solutions.
• Ability to learn, pitch, and demonstrate highly technical products in a fast-changing environment.
• Technical understanding of integrations, APIs, infrastructure management, security, and analytics.
• Experience selling to C-level executives and building new territories using repeatable sales methods.

Nice to have

• Basic understanding of search infrastructure.
• Experience with target-account selling, solution selling, MEDDIC, Challenger, or similar methodologies.

Culture & Benefits

• Remote work with a home office improvement stipend.
• Medical, vision, and dental coverage.
• Generous time-off policy and a 401(k) contribution plan.
• Annual education and wellness stipends.
• Regular company events and daily healthy lunches.
• Inclusive and diverse workplace commitment.

Hiring process

• Complete a brief AI-focused exercise or discussion during the interview process.